Networking, Marketing, Sales, Business Coach

EP47: Shawn Derby Half Million Dollar Painting Business in Just 2 Years Shooting for $1.5M

SUMMARY:

In this episode of the DYB Podcast, Steve shares the mic with Shawn Derby of Sir Paints a Lot, a painting business that set its roots in Montana and flourished in Oregon.

Shawn discusses the different elements that turned his high school gig into a successful business, including faith, love for his family, and a work culture that empowers his employees.

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WHAT YOU’LL LEARN:

– Leadership and Team-Building Tips
– How to build an exceptional culture that empowers employees
– The role of marriage and family in the success of a business
– How to plan the path forward to tripling revenue in 2019

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LISTEN HERE:

QUOTES:

[03:22] “You just don’t hire the first person that you like in an interview. You need to vet them and make sure they have a hunger and a drive to get a job done even if it’s not something that they don’t particularly enjoy.”

[25:14] “I think the biggest paradigm shift has been switching my mind from a technician’s background… and really working on your business and trying to empower people to make the choices themselves and let this be their success.”

[26:21] “If you’re just directing them, all they are is a bunch of go here, go there people. You’re not going to deliver the right experience if you have to tell your crew lead to talk to your client and make sure they’re happy.”

[38:07] “These books that these authors write really are peering into the minds of these geniuses so I’ve been digging through every book I possibly can.”

[39:10] “Take pause, capture at least three takeaways and implement them.”

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HIGHLIGHTS:

[04:30] Shawn’s life before Sir Paints a Lot
[19:48] Revenue breakdown from year 1 to present
[29:10] A “secret sauce” both Steve and Shawn share
[31:29] Shawn discusses the successful programs that he implemented
[36:57] Shawn targets 1.5 million in revenue
[40:34] Books that had an impact on Shawn

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LINKS & RESOURCES MENTIONED IN THIS EPISODE:

Join DYB

Burnett Growth Team – Virtual Assistance

Estimate Rocket – Estimating software

PEP Cloud – Estimating software
Grasshopper – Phone service

Basecamp – Project management software

GroupMe – Team chatting and segmenting work

Pipedrive – CRM system

Full Focus Planner by Michael Hyatt – Goal-setting planner

The Richest Man in Babylon by George S. Clason

The Go-Giver by Bob Burg

Who’s In Your Room by Dr. Misner

ADDITIONAL FREE RESOURCES:

Schedule Your Free Strategy Call With Steve

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Connect with Shawn Derby on Facebook here

Connect with Nadia Burnett on Facebook here

Connect with Steve on Facebook here

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Here’s the pictured Shawn mentioned at [2:13] when he worked a 24-hour shift, went home for a 4-hour nap and then got right back up and did another 32 hours of sanding cabinets!

 

About the Author

As many of you know, my journey has been one of grit, grace, and transformation. At 19, I was a high school dropout, single father, and struggling paint contractor in Michigan. I later moved to Florida, where I faced both personal and professional hardships. With nothing left to lose, I turned to prayer—and was blessed with a relentless hunger to learn. I devoured books, attended seminars, and discovered better ways to streamline and grow my business—even through the Great Recession (and yes, I did hit the wife lottery along the way!). In 2014, I published How To Double Your Business and later sold the painting business, launching a new chapter: coaching others to grow their businesses. For the past 10 years, I’ve dedicated myself to helping business owners scale through the DYB System, while also drawing from frameworks like EOS, Scaling Up, and The Four Disciplines of Execution. Yet something was still missing—something more adaptive, integrated, and complete. Then I found Pinnacle. After months of research and interviews with other Guides, I joined Pinnacle. Their tools and strategies have exceeded every expectation. Now, as a Pinnacle Business Guide, I help leadership teams implement a custom-tailored operating system that draws from the best in the industry—but flexes with your unique business. It’s a dynamic, proven approach to achieve clarity, momentum, and lasting growth. I’m no longer taking on any more 1:1 coaching clients… Instead, I now specialize in working with visionary business owners who are ready to get their leadership teams aligned—around a clear vision, a focused strategy, and an actionable execution plan. With the tools and process I now have as a Pinnacle Business Guide, I help turn alignment into momentum, and momentum into results. If your business is growing—but your leadership team isn’t fully rowing in the same direction—let’s talk.